#------------------------------------------------------------------------------ #$Date: 2017-07-11 14:26:40 +0300 (Tue, 11 Jul 2017) $ #$Revision: 198632 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/18/7151818.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7151818 loop_ _publ_author_name 'Bradley, Stephen A.' 'Bresnan, Brian J.' 'Draper, Sylvia M.' 'Geraghty, Niall W. A.' 'Jeffares, Mark' 'McCabe, Thomas' 'McMurry, T Brian H' 'O'Brien, John E' _publ_section_title ; Photochemical [2 + 2] cycloaddition reactions of 6-alkenyl-3-phenylcyclohex-2-en-1-ones: using biradical conformation control to account for exceptions to the "rule of five". ; _journal_issue 8 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 2959 _journal_page_last 2968 _journal_paper_doi 10.1039/c0ob01131b _journal_volume 9 _journal_year 2011 _chemical_formula_sum 'C19 H22 O3' _chemical_formula_weight 298.37 _chemical_name_systematic ; ? ; _space_group_IT_number 2 _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core2.1beta.dic _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1beta3 _audit_creation_date 2001-10-10T12:14:38-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 90.769(8) _cell_angle_beta 96.613(10) _cell_angle_gamma 103.792(8) _cell_formula_units_Z 2 _cell_length_a 6.6266(7) _cell_length_b 10.1023(10) _cell_length_c 12.3043(11) _cell_measurement_temperature 293(2) _cell_volume 793.91(14) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0183 _diffrn_reflns_av_sigmaI/netI 0.0214 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 2133 _diffrn_reflns_theta_full 21.97 _diffrn_reflns_theta_max 21.97 _diffrn_reflns_theta_min 1.67 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_T_max 0.9836 _exptl_absorpt_correction_T_min 0.9755 _exptl_absorpt_correction_type multi-scan _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.157 _refine_diff_density_min -0.134 _refine_diff_density_rms 0.037 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 287 _refine_ls_number_reflns 1926 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.086 _refine_ls_R_factor_all 0.0523 _refine_ls_R_factor_gt 0.0373 _refine_ls_shift/su_max 0.133 _refine_ls_shift/su_mean 0.021 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0919 _refine_ls_wR_factor_ref 0.1003 _reflns_number_gt 1578 _reflns_number_total 1926 _reflns_threshold_expression >2sigma(I) _cod_data_source_file c0ob01131b.txt _cod_data_source_block bscbs _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'multi-scans' was replaced with the value 'multi-scan' as specified in the replacement file 'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'. Automatic conversion script Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius ; _cod_database_code 7151818 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O3 O 0.2442(2) 0.47824(14) 0.12640(11) 0.0561(4) Uani 1 1 d . . . O2 O -0.0841(2) 0.20970(18) 0.13631(13) 0.0683(5) Uani 1 1 d . . . O1 O 0.2688(3) 0.36697(17) -0.02735(13) 0.0677(5) Uani 1 1 d . . . C6 C 0.2855(3) 0.25449(19) 0.14522(16) 0.0421(5) Uani 1 1 d . . . C5 C 0.4742(3) 0.3077(2) 0.23437(18) 0.0480(6) Uani 1 1 d . . . C4 C 0.4113(4) 0.3378(2) 0.34490(17) 0.0484(6) Uani 1 1 d . . . C3 C 0.2645(3) 0.2162(2) 0.39009(16) 0.0454(5) Uani 1 1 d . . . C2 C 0.3392(5) 0.0816(3) 0.3927(2) 0.0645(7) Uani 1 1 d . . . C1 C 0.1519(4) 0.0118(2) 0.3101(2) 0.0609(7) Uani 1 1 d . . . C9 C 0.1823(6) -0.0615(3) 0.2066(3) 0.0815(9) Uani 1 1 d . . . C8 C 0.3522(6) 0.0104(3) 0.1390(3) 0.0808(10) Uani 1 1 d . . . C7 C 0.3143(5) 0.1325(2) 0.0767(2) 0.0622(7) Uani 1 1 d . . . C11 C 0.0781(3) 0.20702(19) 0.19210(16) 0.0437(5) Uani 1 1 d . . . C10 C 0.0791(3) 0.1480(2) 0.30222(16) 0.0450(5) Uani 1 1 d . . . C12 C 0.2639(3) 0.3693(2) 0.06946(17) 0.0463(5) Uani 1 1 d . . . C13 C 0.2398(5) 0.6003(3) 0.0665(3) 0.0643(7) Uani 1 1 d . . . C14 C 0.2032(4) 0.2602(2) 0.49729(16) 0.0516(6) Uani 1 1 d . . . C15 C 0.0310(5) 0.3133(2) 0.5016(2) 0.0643(7) Uani 1 1 d . . . C16 C -0.0143(7) 0.3630(3) 0.5991(3) 0.0857(9) Uani 1 1 d . . . C17 C 0.1118(9) 0.3604(3) 0.6935(3) 0.1019(13) Uani 1 1 d . . . C18 C 0.2829(8) 0.3098(4) 0.6921(2) 0.1027(13) Uani 1 1 d . . . C19 C 0.3297(5) 0.2577(3) 0.5951(2) 0.0771(8) Uani 1 1 d . . . H10 H -0.057(3) 0.1414(19) 0.3244(15) 0.045(5) Uiso 1 1 d . . . H5A H 0.555(3) 0.235(2) 0.2402(17) 0.058(6) Uiso 1 1 d . . . H5B H 0.561(3) 0.388(2) 0.2084(16) 0.055(6) Uiso 1 1 d . . . H4A H 0.337(3) 0.417(2) 0.3390(16) 0.055(6) Uiso 1 1 d . . . H4B H 0.536(4) 0.364(2) 0.3962(18) 0.057(6) Uiso 1 1 d . . . H7A H 0.430(4) 0.167(2) 0.038(2) 0.070(7) Uiso 1 1 d . . . H7B H 0.187(5) 0.104(3) 0.024(2) 0.090(10) Uiso 1 1 d . . . H1 H 0.051(4) -0.051(2) 0.3470(18) 0.064(7) Uiso 1 1 d . . . H2A H 0.475(4) 0.088(2) 0.366(2) 0.075(8) Uiso 1 1 d . . . H2B H 0.344(4) 0.042(3) 0.462(2) 0.073(7) Uiso 1 1 d . . . H15 H -0.059(4) 0.319(2) 0.437(2) 0.065(7) Uiso 1 1 d . . . H8A H 0.366(4) -0.052(3) 0.084(2) 0.090(8) Uiso 1 1 d . . . H8B H 0.490(5) 0.037(3) 0.190(3) 0.102(11) Uiso 1 1 d . . . H19 H 0.453(4) 0.220(3) 0.589(2) 0.080(9) Uiso 1 1 d . . . H9A H 0.032(5) -0.080(3) 0.163(3) 0.103(11) Uiso 1 1 d . . . H9B H 0.215(4) -0.148(3) 0.230(2) 0.100(9) Uiso 1 1 d . . . H13B H 0.182(6) 0.575(4) -0.015(3) 0.133(12) Uiso 1 1 d . . . H13A H 0.374(6) 0.658(4) 0.076(3) 0.124(12) Uiso 1 1 d . . . H13C H 0.124(7) 0.635(4) 0.089(3) 0.145(14) Uiso 1 1 d . . . H18 H 0.374(6) 0.302(4) 0.751(3) 0.126(13) Uiso 1 1 d . . . H16 H -0.147(6) 0.401(4) 0.595(3) 0.127(13) Uiso 1 1 d . . . H17 H 0.085(5) 0.392(3) 0.766(3) 0.115(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O3 0.0771(11) 0.0467(9) 0.0513(9) 0.0105(7) 0.0160(7) 0.0240(7) O2 0.0458(10) 0.0936(13) 0.0614(10) 0.0149(9) 0.0004(8) 0.0109(8) O1 0.0886(12) 0.0802(12) 0.0421(10) 0.0096(8) 0.0147(8) 0.0323(9) C6 0.0444(12) 0.0402(11) 0.0428(11) 0.0023(9) 0.0101(9) 0.0105(9) C5 0.0420(13) 0.0469(13) 0.0573(14) 0.0103(11) 0.0108(10) 0.0123(11) C4 0.0438(13) 0.0509(13) 0.0456(12) 0.0033(10) -0.0010(11) 0.0048(11) C3 0.0475(12) 0.0450(12) 0.0431(12) 0.0062(9) 0.0027(9) 0.0110(10) C2 0.0738(18) 0.0597(15) 0.0693(17) 0.0243(13) 0.0167(15) 0.0297(13) C1 0.0788(18) 0.0382(12) 0.0657(15) 0.0067(11) 0.0246(14) 0.0064(12) C9 0.125(3) 0.0398(14) 0.086(2) 0.0049(14) 0.048(2) 0.0171(16) C8 0.121(3) 0.0452(15) 0.091(2) 0.0035(15) 0.054(2) 0.0284(16) C7 0.0782(19) 0.0485(14) 0.0658(16) -0.0001(12) 0.0352(16) 0.0144(13) C11 0.0436(13) 0.0426(12) 0.0437(12) -0.0025(9) 0.0050(10) 0.0086(10) C10 0.0415(13) 0.0456(12) 0.0465(12) 0.0005(9) 0.0104(10) 0.0053(10) C12 0.0444(13) 0.0519(13) 0.0439(13) 0.0023(10) 0.0095(10) 0.0123(10) C13 0.0670(18) 0.0513(14) 0.0787(19) 0.0232(13) 0.0126(15) 0.0194(14) C14 0.0631(15) 0.0446(12) 0.0399(12) 0.0067(9) 0.0057(11) -0.0010(11) C15 0.090(2) 0.0564(15) 0.0501(15) 0.0041(11) 0.0178(14) 0.0207(14) C16 0.128(3) 0.0584(17) 0.073(2) -0.0026(14) 0.048(2) 0.0109(17) C17 0.145(4) 0.073(2) 0.064(2) -0.0148(16) 0.045(2) -0.036(2) C18 0.122(3) 0.109(3) 0.0382(18) 0.0015(17) -0.003(2) -0.042(2) C19 0.076(2) 0.087(2) 0.0520(17) 0.0094(13) -0.0019(14) -0.0077(16) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 O3 C13 117.04(18) . . ? C12 C6 C11 107.22(16) . . ? C12 C6 C7 108.90(17) . . ? C11 C6 C7 106.80(18) . . ? C12 C6 C5 108.91(16) . . ? C11 C6 C5 113.17(16) . . ? C7 C6 C5 111.67(19) . . ? C4 C5 C6 113.58(18) . . ? C5 C4 C3 113.79(19) . . ? C14 C3 C4 109.11(17) . . ? C14 C3 C2 115.08(18) . . ? C4 C3 C2 115.42(19) . . ? C14 C3 C10 115.47(17) . . ? C4 C3 C10 111.32(16) . . ? C2 C3 C10 89.44(16) . . ? C1 C2 C3 90.89(18) . . ? C9 C1 C2 121.0(3) . . ? C9 C1 C10 120.0(2) . . ? C2 C1 C10 90.02(16) . . ? C1 C9 C8 118.3(2) . . ? C7 C8 C9 117.2(3) . . ? C8 C7 C6 116.8(2) . . ? O2 C11 C10 121.55(19) . . ? O2 C11 C6 119.53(18) . . ? C10 C11 C6 118.74(18) . . ? C11 C10 C3 116.69(17) . . ? C11 C10 C1 114.82(17) . . ? C3 C10 C1 89.55(16) . . ? O1 C12 O3 123.2(2) . . ? O1 C12 C6 126.11(19) . . ? O3 C12 C6 110.62(17) . . ? C15 C14 C19 117.2(3) . . ? C15 C14 C3 122.2(2) . . ? C19 C14 C3 120.4(2) . . ? C14 C15 C16 121.7(3) . . ? C17 C16 C15 120.2(4) . . ? C18 C17 C16 119.7(3) . . ? C17 C18 C19 121.0(3) . . ? C14 C19 C18 120.2(4) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O3 C12 1.337(2) . ? O3 C13 1.449(3) . ? O2 C11 1.213(2) . ? O1 C12 1.195(2) . ? C6 C12 1.520(3) . ? C6 C11 1.526(3) . ? C6 C7 1.545(3) . ? C6 C5 1.550(3) . ? C5 C4 1.515(3) . ? C4 C3 1.529(3) . ? C3 C14 1.516(3) . ? C3 C2 1.554(3) . ? C3 C10 1.557(3) . ? C2 C1 1.531(4) . ? C1 C9 1.522(3) . ? C1 C10 1.564(3) . ? C9 C8 1.526(4) . ? C8 C7 1.518(4) . ? C11 C10 1.487(3) . ? C14 C15 1.378(3) . ? C14 C19 1.390(3) . ? C15 C16 1.386(4) . ? C16 C17 1.355(5) . ? C17 C18 1.352(5) . ? C18 C19 1.394(5) . ?